Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane

2019 ◽  
Vol 9 (15) ◽  
pp. 3874-3878 ◽  
Author(s):  
Wubing Yao ◽  
Rongrong Li ◽  
Jianguo Yang ◽  
Feiyue Hao
Keyword(s):  
Transition Metal ◽  
Reductive Cleavage ◽  
Metal Free ◽  
Free Process ◽  
Tertiary Amides ◽  
Current Systems

The first hydride-catalyzed reductive cleavage of tertiary amides using the hydrosilane as reducing reagent has been developed. This transition-metal-free process may offer a versatile alternative to current systems for the selective reductive cleavage of amides.

Electrochemical-induced synthesis of quinazolinones via cathode hydration of o-aminobenzonitriles in aqueous solution

2021 ◽  
Author(s):  
Li Yang ◽  
Huiqing Hou ◽  
Lan Li ◽  
Jin Wang ◽  
Sunying Zhou ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Transition Metal ◽  
Metal Free ◽  
Free Process

An efficient and practical electrochemical-catalyzed transition metal-free process for the synthesis of substituted quinazolinones from simple and readily available o-aminobenzonitriles and aldehydes in water has been accomplished. I2/base and water...

Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling

Synthesis ◽  
2021 ◽  
Author(s):  
Yury N. Kotovshchikov ◽  
Stepan S. Tatevosyan ◽  
Gennadij V. Latyshev ◽  
Nikolay V. Lukashev ◽  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Cost Effective ◽  
Reductive Cleavage ◽  
Effective Procedure ◽  
Free Base ◽  
Metal Free ◽  
Fused Heterocycles ◽  
Convenient Approach

AbstractA convenient approach to assemble 1,2,3-triazole-fused 4H-3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C–O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C–I bond was achieved by the use of Na2CO3 in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.

Hydride-Induced Anionic Cyclization: An Efficient Method for the Synthesis of 6-H-Phenanthridines via a Transition-Metal-Free Process

2015 ◽  
Vol 17 (6) ◽  
pp. 1613-1616 ◽  
Author(s):  
Wei-Lin Chen ◽  
Chun-Yuan Chen ◽  
Yan-Fu Chen ◽  
Jen-Chieh Hsieh
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Metal Free ◽  
Free Process

scholarly journals An Electroreductive Approach to Silyl Radical Chemistry via Strong Si–Cl Bond Activation

2020 ◽  
Author(s):  
Lingxiang Lu ◽  
Juno Siu ◽  
Yihuan Lai ◽  
Song Lin
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Reductive Cleavage ◽  
Materials Chemistry ◽  
Metal Free ◽  
Silyl Radical ◽  
Silyl Radicals ◽  
New Strategy ◽  
Radical Generation ◽  
Synthetic Medicinal

The construction of C(sp<sup>3</sup>)–Si bonds is important in synthetic, medicinal, and materials chemistry. In this context, reactions mediated by silyl radicals have become increasingly attractive but methods for accessing these intermediates remain limited. We present a new strategy for silyl radical generation via electroreduction of readily available chlorosilanes. At highly biased potentials, electrochemistry grants access to silyl radicals through energetically uphill reductive cleavage of strong Si–Cl bonds. This strategy proved to be general in various alkene silylation reactions including disilylation, hydrosilylation, and allylic silylation under simple and transition-metal-free conditions.

ChemInform Abstract: An Efficient, Transition-Metal-Free Process for the Synthesis of Substituted Dihydrofurans via a Michael/Cyclization Tandem Reaction.

ChemInform ◽  
2011 ◽  
Vol 42 (20) ◽  
pp. no-no
Author(s):  
Ming-Yu Wu ◽  
Ming-Qi Wang ◽  
Kun Li ◽  
Xing-Wen Feng ◽  
Ting He ◽  
...  
Keyword(s):  
Transition Metal ◽  
Tandem Reaction ◽  
Metal Free ◽  
Free Process

scholarly journals An Electroreductive Approach to Silyl Radical Chemistry via Strong Si–Cl Bond Activation

2020 ◽  
Author(s):  
Lingxiang Lu ◽  
Juno Siu ◽  
Yihuan Lai ◽  
Song Lin
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Reductive Cleavage ◽  
Materials Chemistry ◽  
Metal Free ◽  
Silyl Radical ◽  
Silyl Radicals ◽  
New Strategy ◽  
Radical Generation ◽  
Synthetic Medicinal

The construction of C(sp<sup>3</sup>)–Si bonds is important in synthetic, medicinal, and materials chemistry. In this context, reactions mediated by silyl radicals have become increasingly attractive but methods for accessing these intermediates remain limited. We present a new strategy for silyl radical generation via electroreduction of readily available chlorosilanes. At highly biased potentials, electrochemistry grants access to silyl radicals through energetically uphill reductive cleavage of strong Si–Cl bonds. This strategy proved to be general in various alkene silylation reactions including disilylation, hydrosilylation, and allylic silylation under simple and transition-metal-free conditions.

ChemInform Abstract: A One-Pot Synthetic Strategy for Construction of the Dibenzodiazepine Skeleton via a Transition Metal-Free Process.

ChemInform ◽  
2015 ◽  
Vol 46 (6) ◽  
pp. no-no
Author(s):  
Shuai Fang ◽  
Xiaoyi Niu ◽  
Zeyuan Zhang ◽  
Yan Sun ◽  
Xiaomeng Si ◽  
...  
Keyword(s):  
Transition Metal ◽  
One Pot ◽  
Metal Free ◽  
Synthetic Strategy ◽  
Free Process

An efficient, transition-metal-free process for the synthesis of substituted dihydrofurans via a Michael/cyclization tandem reaction

2011 ◽  
Vol 52 (6) ◽  
pp. 679-683 ◽  
Author(s):  
Ming-Yu Wu ◽  
Ming-Qi Wang ◽  
Kun Li ◽  
Xing-Wen Feng ◽  
Ting He ◽  
...  
Keyword(s):  
Transition Metal ◽  
Tandem Reaction ◽  
Metal Free ◽  
Free Process

scholarly journals Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes

2020 ◽  
Vol 11 (30) ◽  
pp. 8020-8024 ◽  
Author(s):  
Feng Shen ◽  
Long Lu ◽  
Qilong Shen
Keyword(s):  
Transition Metal ◽  
Good Yield ◽  
Metal Free ◽  
Free Process ◽  
Boronic Esters

A transition metal free process for conjunctive functionalization of alkenylboron ate-complexes with electrophilic fluoroalkylthiolating reagents affords β-tri- and difluoroalkylthiolated boronic esters in good yield and diastereoselectivity.

scholarly journals An Electroreductive Approach to Silyl Radical Chemistry via Strong Si–Cl Bond Activation

2020 ◽  
Author(s):  
Lingxiang Lu ◽  
Juno Siu ◽  
Yihuan Lai ◽  
Song Lin
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Reductive Cleavage ◽  
Materials Chemistry ◽  
Metal Free ◽  
Silyl Radical ◽  
Silyl Radicals ◽  
New Strategy ◽  
Radical Generation ◽  
Synthetic Medicinal

The construction of C(sp<sup>3</sup>)–Si bonds is important in synthetic, medicinal, and materials chemistry. In this context, reactions mediated by silyl radicals have become increasingly attractive but methods for accessing these intermediates remain limited. We present a new strategy for silyl radical generation via electroreduction of readily available chlorosilanes. At highly biased potentials, electrochemistry grants access to silyl radicals through energetically uphill reductive cleavage of strong Si–Cl bonds. This strategy proved to be general in various alkene silylation reactions including disilylation, hydrosilylation, and allylic silylation under simple and transition-metal-free conditions.

Sign in / Sign up

Export Citation Format

Share Document